Sodium Hydroxide → (1H-indol-5-yl)methanol

Participants

Reaction Steps

Indole-5-carboxylic acid (5.02 g, 31.3 mmol) in tetrahydrofuran (40 mL) was added slowly to the lithium aluminium hydride (1.88 g, 49.5 mmol) stirred in tetrahydrofuran (125 mL) under nitrogen with external heating so as to maintain a gently reflux. The mixture was heated at reflux for 2 hours and cooled to room temperature. 2 N sodium hydroxide (10 mL) was then added dropwise to the reaction mixture. The precipitate was removed by filtration and the filtrate was concentrated. It was dissolved in dichloromethane (80 mL), washed with 2 N sodium hydroxide (10 mL), water (20 mL) and brine (20 mL), dried over anhydrous sodium sulfate and concentrated to give about 5 g of (1H-indol-5-yl)-methanol.

Provenance & Evidence